NP-MRD: Showing NP-Card for 5-Androstene-3alpha,16beta,17beta-triol (NP0339209)

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Record Information

Version

2.0

Created at

2024-09-11 20:25:32 UTC

Updated at

2024-09-11 20:25:32 UTC

NP-MRD ID

NP0339209

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Androstene-3alpha,16beta,17beta-triol

Description

5-Androstene-3alpha-16b,17b-triol, also known as 3-hydroxy-9(Z)-octadecenoylcarnitine, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. 5-Androstene-3alpha-16b,17b-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208182D          

 22 25  0  0  1  0            999 V2000
    8.1395  -10.1833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1395  -11.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4249   -9.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4249  -11.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105  -10.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105  -11.0083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5684  -10.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684  -11.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539   -9.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539  -11.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2830   -8.9458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2830   -9.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684   -8.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8540   -8.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0676   -8.6908    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5525   -9.3583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0677  -10.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9960  -11.4208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3775   -9.3582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3225   -7.9062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395   -9.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3693   -8.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 10  2  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  7 12  1  0  0  0  0
 14 13  1  0  0  0  0
  9  7  1  0  0  0  0
  9 14  1  0  0  0  0
 15 11  1  0  0  0  0
 12 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
  6 18  1  6  0  0  0
 16 19  1  1  0  0  0
 15 20  1  1  0  0  0
  1 21  1  1  0  0  0
 11 22  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0339209

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CCC3C(CC=C4C[C@H](O)CC[C@]34C)C1C[C@H](O)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-17,20-22H,4-10H2,1-2H3/t12-,13?,14?,15?,16+,17+,18+,19+/m1/s1

> <INCHI_KEY>
GUGSXATYPSGVAY-YAUITSCLSA-N

> <FORMULA>
C19H30O3

> <MOLECULAR_WEIGHT>
306.4397

> <EXACT_MASS>
306.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.372517805101566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,5R,13S,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,13,14-triol

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
1.723273742666667

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.159249456373555

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.623893402267957

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972437702926341

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
86.8427

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5R,13S,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,13,14-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      15.194 -19.009   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.194 -20.549   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.860 -18.239   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.860 -21.319   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.526 -19.009   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.526 -20.549   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.861 -19.009   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.861 -20.549   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.527 -18.239   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.527 -21.319   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.195 -16.699   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.195 -18.239   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.861 -15.929   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.527 -16.699   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.660 -16.223   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.565 -17.469   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.660 -18.715   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.193 -21.319   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      23.105 -17.469   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      21.135 -14.758   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      15.194 -17.469   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.356 -15.167   0.000  0.00  0.00           C+0
CONECT    1    3    9    2   21                                             
CONECT    2    4   10    1                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   18                                                  
CONECT    7    8   12    9                                                  
CONECT    8    7   10                                                       
CONECT    9    1    7   14                                                  
CONECT   10    8    2                                                       
CONECT   11   13   15   12   22                                             
CONECT   12    7   11   17                                                  
CONECT   13   11   14                                                       
CONECT   14   13    9                                                       
CONECT   15   11   16   20                                                  
CONECT   16   15   17   19                                                  
CONECT   17   12   16                                                       
CONECT   18    6                                                            
CONECT   19   16                                                            
CONECT   20   15                                                            
CONECT   21    1                                                            
CONECT   22   11                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
5-Androstene-3a-16b,17b-triol	Generator
5-Androstene-3α-16b,17b-triol	Generator

Chemical Formula

C₁₉H₃₀O₃

Average Mass

306.4397 Da

Monoisotopic Mass

306.21949 Da

IUPAC Name

(2R,5R,13S,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,13,14-triol

Traditional Name

(2R,5R,13S,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,13,14-triol

CAS Registry Number

Not Available

SMILES

C[C@]12CCC3C(CC=C4C[C@H](O)CC[C@]34C)C1C[C@H](O)[C@@H]2O

InChI Identifier

InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-17,20-22H,4-10H2,1-2H3/t12-,13?,14?,15?,16+,17+,18+,19+/m1/s1

InChI Key

GUGSXATYPSGVAY-YAUITSCLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
16-beta-hydroxysteroid
16-hydroxysteroid
3-alpha-hydroxysteroid
17-hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Polyol
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.17	ALOGPS
logP	1.72	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.84 m³·mol⁻¹	ChemAxon
Polarizability	35.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013199

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029327

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481647

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5-Androstene-3alpha,16beta,17beta-triol (NP0339209)

MOL for NP0339209 (5-Androstene-3alpha,16beta,17beta-triol)

3D MOL for NP0339209 (5-Androstene-3alpha,16beta,17beta-triol)

3D SDF for NP0339209 (5-Androstene-3alpha,16beta,17beta-triol)

3D-SDF for NP0339209 (5-Androstene-3alpha,16beta,17beta-triol)

PDB for NP0339209 (5-Androstene-3alpha,16beta,17beta-triol)

3D PDB for NP0339209 (5-Androstene-3alpha,16beta,17beta-triol)

SMILES for NP0339209 (5-Androstene-3alpha,16beta,17beta-triol)

INCHI for NP0339209 (5-Androstene-3alpha,16beta,17beta-triol)

Structure for NP0339209 (5-Androstene-3alpha,16beta,17beta-triol)

3D Structure for NP0339209 (5-Androstene-3alpha,16beta,17beta-triol)